Triethylamine → N-((Methoxycarbonyl)methyl)4-Nitrophenylalanine Methyl Ester

HRID 719663노트

반응식

HRID 719663 반응식
C(N(CC)CC)C.Cl.[CH3:9][O:10][C:11](=[O:24])[C@H:12]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1)[NH2:13].[CH3:25][O:26][C:27](=[O:30])[CH2:28]Br>C1COCC1>[CH3:9][O:10][C:11](=[O:24])[C@H:12]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1)[NH:13][CH2:28][C:27]([O:26][CH3:25])=[O:30]

참가 물질

5

반응물 3

HCID 8471Triethylamine2회HCID 60984Methyl bromoacetateHCID 11715866Methyl 4-nitro-L-phenylalaninate hydrochloride

생성물 1

HCID 68574020N-((Methoxycarbonyl)methyl)4-Nitrophenylalanine Methyl Ester수율 92%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Triethylamine (22 mmol) was added to a suspension of 4-Nitrophenylalanine methyl ester hydrochloride (2) (21 mmol) in THF (50 ml). The mixture was stirred at room temperature for one hour, the triethylamine hydrochloride was filtered off, and the filtrate concentrated to yellow oil. The oil was dissolved in dry THF (50 ml) and to this solution was added triethylamine (60 mmol) and methylbromoacetate (60 mmol), the solution was stirred at room temperature under nitrogen atmosphere for 3 hours, after which the precipitate was filtered off and the filtrate concentrated on vacuum. The residue was dissolved in ethylacetate, washed with H2O, dried (MgSO4) and concentrated on vacuum to give yellow oil. The yield was 92%.

후처리

  1. filtrationthe triethylamine hydrochloride was filtered off
  2. concentrationthe filtrate concentrated to yellow oil
  3. dissolutionThe oil was dissolved in dry THF (50 ml) and to this solution
  4. stirringthe solution was stirred at room temperature under nitrogen atmosphere for 3 hours
  5. filtrationafter which the precipitate was filtered off
  6. concentrationthe filtrate concentrated on vacuum
  7. dissolutionThe residue was dissolved in ethylacetate
  8. washwashed with H2O
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated on vacuum
  11. customto give yellow oil

출처 및 근거

ORD 기록
ord-1d361a77553743f0b595134964d1542c
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07132513B2

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